Highly beta-selective C-allylation of a ribofuranoside controlling steric hindrance in the transition state.
A highly beta-selective C-allylation of 2,3-O-(3-pentylidene)-D-ribofuranosyl fluoride is described. This strategy will provide a new concept for synthesizing beta-C-ribosides by controlling the effect of steric hindrance in the transition state.
Ichikawa
Satoshi
S
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan. ichikawa@pharm.hokudai.ac.jp
Hayashi
Ryoko
R
Hirano
Shinpei
S
Matsuda
Akira
A
D000475:Alkenes / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
C533648:2,3-O-(3-pentylidene)-D-ribofuranosyl fluoride; D000475:Alkenes; D009005:Monosaccharides; D005459:Fluorides